How to Hook Up on a Trip

Flight attendant Heather Poole was impressed that one of her business class passengers really seemed to have it together. He was polite and knew how to take care of himself.

So she married him.

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There’s a bit more to the story, of course. They exchanged phone numbers as the flight deplaned and their courtship took a while to play out, but Poole recalls her first impression of her now-husband of seven years as if it was yesterday.

“Here’s a man with a plan,” Poole remembers, a guy who came prepared with a “pen and paper, magazines, and a beautiful sandwich that he brought from a deli.” On top of which, her husband-to-be was courteous and made eye contact, which in Poole’s experience is not the norm.

A less-subtle kind of love was in the air last October when Air New Zealand ran a matchmaking flight from Los Angeles to Auckland, including a pre-departure mixer at the gate and in-flight speed dating abetted by an open bar. The flight was chaperoned by “The Bachelor” bachelor Jason Mesnick and picked-on-the-show girlfriend Molly Malaney, who are due to be married during a “Bachelor” special this spring. Interviewed in flight, one of Malaney’s tips to passengers was to “be yourself and have fun.”

Somewhere between these two scenarios - the serendipitous love connection and the Love Plane - lies an approach you can likely get on board with while vacationing. Consider the tips herein, whether you’re looking for love, friendship, or ways to make conversation with a stranger, who to paraphrase frequent traveler Will Rogers, is just a friend you haven’t met yet.

Try these ice beakers

“I had the greatest conversation with someone on a shuttle flight recently by asking him what his favorite iPhone apps were,” says nutritionist Monika Woolsey. “It was not a pickup, I'm attached, but it was a great way to get someone talking,” she says.

When Vacation Gals co-founder Beth Blair was a flight attendant, she witnessed passengers offering to buy each other drinks and at times “someone would ask me to ask a passenger if he or she was single. Every so often they were and the pair would end up standing in the aisle or galley chatting or would exchange business cards.”

A good prop can break the ice, too. “When sitting on a train or bus, carry two newspapers: one from your hometown and one from the local area,” suggests tour guide Ann Lombardi, co-owner of the Trip Chicks. “For me, that has always been a "Where are you from?" conversation starter."

San Diego food writer Maria Hunt of the bubblygirl.com finds that asking about what someone’s “eating or drinking is a natural opener,” and quite simply “saying ‘hi’ and smiling works if you are a woman.”

Talk, don’t stalk

If you’re a guy making small talk, be mindful of how your questions are coming across to the ladies. “Rather than ask ‘Where are you staying?’ ask, ‘What neighborhood or part of town are you staying in?’ suggests travel and style writer Jennifer Paull. “I've known some travelers, women on their own particularly, who get guarded if they think someone's trying to pinpoint their location. An easy rephrase ensures that there aren't any stalker-ish interpretations of an innocuous question.

Pass notes in (first, business, or economy) class

One of Blair’s fondest memories as a flight attendant “was when a young man asked for an extra cocktail napkin and then sent a ‘love note’ to a passenger several rows ahead asking if she was available. I'll never forget the passengers tapping each other and saying, ‘Pass this to 13 B.’ It was like passing notes in school. The girl sent back a ‘Yes, I'm a single’ note. The man traded seats with her seatmate and they spent the rest of the flight chatting.”

Be nice to your classmates

When probed for tips aboard last year’s matchmaking flight, bachelor Mesnick repeated something he told his four-year-old son: “Why don’t you go and try to play with every kid in your class for a couple minutes?” which, given the rigors of winnowing down potential mates on a reality show or speed dating on an aircraft, is not bad advice. Even if you’d rather not play a volume game, Lombardi observes that showing “curiosity and appreciation” and loosening up a little can’t hurt your case. “A person is more likely to strike up a conversation with a happy-faced visitor than one with a scowl or frown,” she says.

Let your schedule go

While she typically follows an itinerary and timetable in the 88 countries she’s toured, Lombardi says her fondest travel moments have been unplanned. “If your every waking minute is etched in stone during a trip, you may miss a super experience or a chance to make a new pal,” she says. “Have a flexible schedule, if possible, and leave room for savoring surprises during your trip. If you're invited to a festival, religious ceremony, or wedding, just go.”

Go to the mountain

Winter sports provide travelers with easy ways to get acquainted, suggests travel writer Georgia de Katona of bohemenjetset.com. “For women, meeting men on a ski or snowboard hill is so easy it's almost ridiculous,” she says, often inspiring such lines as "Can I ride up with you?” or “What trails are you riding today?” or “Do you know this mountain?” Katona adds that she and her husband “snowboard together on all kinds of runs, but if he's more than two feet away from me in a lift line, a man will start a conversation with me,” she says, noting that “It's so friendly and it's really safe.”

Send regards

If saying hello is a challenge, try saying hello for someone else. Before leaving home, “ask friends, co-workers, or family if there's anyone they'd like you to look up for them,” Lombardi says. “I have a wonderful time extending greetings on behalf of others. I’ve crossed paths with a neighbor's distant relative in rural Switzerland, my aunt's feisty 88-year-old pen pal in Korea, and many more colorful characters while I traveled.”

Make sure your relationship isn't too close

Blair’s recalls the time “two passengers in their twenties were sitting together and really seemed to hit it off.” At one point during the flight, Blair heard a burst of laughter erupt from the couple. “They had just discovered they were going to the same wedding. Their parents were getting married - to each other. That's another couple I still wonder about.”